1. Field of the Invention
The present invention relates to an azomethine yellow dye compound having an aryl group bonded to a carbon atom in an azomethine moiety thereof, which is useful as yellow dye for silver halide photographic photosensitive materials, yellow dye for printing materials used in inkjet or thermal transfer printing or the like, yellow dye for toner in electrophotography, yellow dye for prints, yellow dye for color proofs, yellow dye for optical memory media, yellow dye for organic electroluminescence elements, filter dye for solid-state image pickup tubes or color liquid-crystal televisions, and also as an intermediate in the production thereof.
2. Description of the Related Art
Many types of yellow azomethine dyes are generally known and are used as yellow dye compounds used for silver halide photographic photosensitive materials and also as dyes or colorants for other various purposes. Especially for silver halide photographic photosensitive materials, azomethine dyes having an aniline derivative bonded to the nitrogen atom in an azomethine moiety thereof and having an acyl group, a carbamoyl group, an alkoxycarbonyl group or the like bonded to a carbon atom in said moiety are widely known. These dyes can be formed by reacting an active methylene compound (generally a yellow coupler) provided in a silver halide photographic photosensitive material with an oxide product of a p-phenylenediamine based developing agent when the photographic photosensitive material is developed, and these dyes have been used as photographic dye.
However, these yellow azomethine dyes are problematic in that an absorption coefficient thereof is small and a hydrolysis stability thereof against acid is low. As one means for solving these problems, use of azomethine yellow dye compounds having an aryl group and a carbamoyl group both bonded to a carbon atom in an azomethine moiety thereof has been taken into consideration. Some azomethine compounds having an aryl group and a carbamoyl group both bonded to a carbon atom in an azomethine moiety thereof are described in, for example, Farmaco, 54, 39 (1999); Pestic. Sci., 44, 49 (1995); J. Pract. Chem., 128, 1 (1930), Zh. Obshch. Khim., 26, 1169 (1956); and Zh. Obshch. Khim., 26, 2019 (1956). In all of these azomethine dye compounds described therein, however, a nitrogen atom in the carbamoyl group bonded to the carbon atom in the azomethine moiety is bonded to the aryl group that is bonded to the carbon atom in the azomethine moiety either directly or via a linking group, such as carbonyl group, provided therebetween. Further, these dye compounds are still problematic in that a color hue thereof is not good. These azomethine dye compounds described above are not those of a type having a hydrogen atom bonded to the nitrogen atom in the carbamoyl group therein.
On the other hand, some other azomethine compounds having an aryl group and a carbamoyl group, which has a hydrogen atom bonded to a nitrogen atom thereof, with both groups being bonded to a carbon atom in the azomethine moiety thereof, as described, for example, in J. Org. Chem. USSR, 10, 609 (1974); J. Pract. Chem., 114, 332; Tetrahedron Lett., 1967, 3291; Justus Liebigs Ann. Chem., 442, 266 (1926); J. Pract. Chem., 114, 332 (1926); J. Chem. Soc., 1929, 1198; and Bull. Chem. Soc. Jpn., 69, 25 (1996), are known. However, these compounds do not have an amino group at a para-position of a phenyl group bonded to the nitrogen atom in the azomethine moiety thereof, and furthermore, since a maximum absorption wavelength thereof is short, they con not be used as yellow dye.
As described above, an azomethine yellow dye having a p-aminophenyl group bonded to the nitrogen atom in an azomethine moiety thereof, and having an aryl group and a carbamoyl group both bonded to a carbon atom in the azomethine moiety thereof with the carbamoyl group having a hydrogen atom bonded to a nitrogen atom in the carbamoyl group, is completely unknown.
An object of the present invention is to provide an azomethine yellow dye compound that has a large absorption absorption coefficient and is stable against acid hydrolysis. The dye compound has a p-aminophenyl group bonded to a nitrogen atom in an azomethine moiety thereof and has an aryl group and a carbamoyl group both bonded to a carbon atom in the azomethine moiety thereof. The carbamoyl group has a hydrogen atom bonded to a nitrogen atom thereof.
Having assiduously studied the problems noted above, the present inventors have found that these problems can be solved by the following method.
A first aspect of the present invention is an azomethine yellow dye compound represented by the following general formula (I).
General formula (I) 
In the general formula (I), R1 and R2 each independently represent a hydrogen atom or a substituent; R3 represents a a substituent; m indicates an integer from 0 to 3; when m is 2 or greater, R3""s may be the same as or different from each other, and the R3""s may be bonded to each other to form a condensed ring; R3""s may be bonded to R1 or R2 to form a condensed ring; R4 represents an aryl group or a heterocyclic group; R5 and R6 each independently represent a hydrogen atom or a substituent; R7 represents a substituent; n indicates an integer from 0 to 4; and when n is 2 or greater, R7""s may be the same as or different from each other, and the R7""s may be bonded to each other to form a condensed ring; R7 may be bonded to R5 or R6 to form a condensed ring; and R5 and R6 may be bonded to each other to form a ring.
The compound of the present invention, which is represented by the following general formula (I), is described in detail below.
General formula (I) 
In the formula (I), R1 and R2 each independently represent a hydrogen atom or a substituent; R3 represents a substituent; m indicates an integer from 0 to 3; and when m is 2 or greater, R3""s may be the same as or different from each other, and the R3""s may be bonded to each other to form a condensed ring; R3 may be bonded to R1 or R2 to form a condensed ring; R4 represents an aryl group or a heterocyclic group; R5 and R6 each independently represent a hydrogen atom or a substituent; R7 represents a substituent; n indicates an integer from 0 to 4; when n is 2 or greater, R7""s may be the same as or different from each other, and the R7""s may be bonded to each other to form a condensed ring; R7 may be bonded to R5 or R6 to form a condensed ring; and R5 and R6 may be bonded to each other to form a ring. Herein, xe2x80x9csubstituentxe2x80x9d means a substituting group other than a hydrogen atom.
In general formula (I), R1 and R2 each independently represent a hydrogen atom or a substituent. Examples of the substituent include ahalogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic-oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group (examples of which include an alkylamino group, an arylamino group and a heterocyclic amino group), an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkylsulfonylamino group, arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic-thio group, a sulfamoyl group, a sulfo group, an alkylsulfinyl group, arylsulfinyl group, an alkylsulfonyl group, arylsulfonyl group, an aryloxysulfinyl group, an alkoxysulfinyl group, an aryloxysulfonyl group, an alkoxysulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an aryl or heterocyclic-azo group, an imido group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, and a silyl group.
The substituents for R1, R2, R3, R4, R5, R6 and R7 may be further substituted, for example, with any of those groups mentioned above.
More particularly, examples of the substituent for R1 and R2 include halogen atoms (e.g., chlorine, bromine and iodine), an alkyl group (the alkyl group may be a linear or branched, substituted or unsubstituted alkyl group, and the group preferably has from 1 to 30 carbon atoms, e.g., methyl, ethyl, n-propyl, isopropyl, t-butyl, n-octyl, eicosyl, 2-chloroethyl, 2-cyanoethyl and 2-ethylhexyl), a cycloalkyl group [this cycloalkyl group is preferably a substituted or unsubstituted cycloalkyl group having from 3 to 30 carbon atoms, e.g., cyclohexyl, cyclopentyl, 4-n-dodecylcyclohexyl and a polycycloalkyl group having a polycyclic structure, examples of the polycycloalkyl group including a bicycloalkyl group (the bicycloalkyl group is preferably an unsubstituted or substituted group having from 5 to 30 carbon atoms, such as bicyclo[1,2,2]heptan-2-yl or bicyclo[2,2,2]octan-3-yl) and a tricycloalkyl group, and the cycloalkyl group is preferably a monocyclic cycloalkyl group or a bicycloalkyl group, and more preferably a monocyclic cycloalkyl group], an alkenyl group (examples of the alkenyl group include a linear or branded, substituted or unsubstituted alkenyl group preferably having from 2 to 30 carbon atoms, e.g., vinyl, allyl, prenyl, geranyl and oleyl), a cycloalkenyl group [examples of this cycloalkenyl group include substituted or unsubstituted cycloalkenyl groups preferably having from 3 to 30 carbon atoms, e.g., 2-cyclopenten-1-yl and 2-cyclohexen-1-yl, and includes a polycycloalkenyl group having a polycyclic structure, such as, a tricycloalkenyl group and a bicycloalkenyl group (examples of the bicycloalkenyl group include unsubstituted or substituted bicycloalkenyl group, preferably having from 5 to 30 carbon atoms, e.g., bicyclo[2,2,1]hept-2-en-1-yl and bicyclo[2,2,2]oct-2-en-4-yl), and the cycloalkenyl group is preferably a monocyclic cycloalkenyl group or a bicycloalkenyl group, and more preferably a monocyclic cycloalkenyl group], an alkynyl group (examples of the alkynyl group include substituted or unsubstituted alkynyl groups preferably having from 2 to 30 carbon atoms, e.g., ethynyl, propargyl and trimethylsilylethynyl), an aryl group (examples of the aryl group include substituted or unsubstituted aryl groups, preferably having from 6 to 30 carbon atoms, e.g., phenyl, p-tolyl, naphthyl, m-chlorophenyl and o-hexadecanoylaminophenyl), a heterocyclic group (the heterocyclic group is preferably a monovalent group derived from a substituted or unsubstituted, aromatic or non-aromatic, heterocyclic compound, which has 5- or 6-members, by removing one hydrogen atom from the compound, and more preferably the heterocyclic group is a 5-membered or 6-membered aromatic heterocyclic group having from 3 to 30 carbon atoms, e.g., 2-furyl, 2-thienyl, 2-pyrimidinyl and 2-benzothiazolyl), a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkoxy group (examples of the alkoxy group include substituted or unsubstituted alkoxy groups, preferably having from 1 to 30 carbon atoms, e.g., methoxy, ethoxy, isopropoxy, t-butoxy, n-octyloxy and 2-methoxyethoxy), an aryloxy group (examples of the aryloxy group include substituted or unsubstituted aryloxy groups, preferably having from 6 to 30 carbon atoms, e.g., phenoxy, 2-methylphenoxy, 4-t-butylphenoxy, 3-nitrophenoxy and 2-tetradecanoylaminophenoxy), a silyloxy group (the silyloxy group preferably has from 3 to 20 carbon atoms, e.g., trimethylsilyloxy and t-butyldimethylsilyloxy), a heterocyclic-oxy group (examples of the heterocyclic-oxy group include substituted or unsubstituted heterocyclic-oxy groups preferably having from 2 to 30 carbon atoms, e.g., 1-phenyltetrazol-5-oxy and 2-tetrahydropyranyloxy), an acyloxy group (preferable examples of the acyloxy group include a formyloxy group, a substituted or unsubstituted alkylcarbonyloxy group having from 2 to 30 carbon atoms, and a substituted or unsubstituted aryloxycarbonyl group having from 6 to 30 carbon atoms, e.g., formyloxy, acetyloxy, pivaloyloxy, stearoyloxy, benzoyloxy, and p-methoxyphenylcarbonyloxy), a carbamoyloxy group (examples of the carbamoyloxy group include substituted or unsubstituted carbamoyloxy groups preferably having from 1 to 30 carbon atoms, e.g., N,N-dimethylcarbamoyloxy, N,N-diethylcarbamoyloxy, morpholinocarbonyloxy, N,N-di-n-octylaminocarbonyloxy and N-n-octylcarbamoyloxy), an alkoxycarbonyloxy group (examples of the alkoxycarbonyloxy group include substituted or unsubstituted alkoxycarbonyloxy groups preferably having from 2 to 30 carbon atoms, e.g., methoxycarbonyloxy, ethoxycarbonyloxy, t-butoxycarbonyloxy and n-octylcarbonyloxy), an aryloxycarbonyloxy group (examples of the aryloxycarbonyloxy group include substituted or unsubstituted aryloxycarbonyloxy groups preferably having from 7 to 30 carbon atoms, e.g., phenoxycarbonyloxy, p-methoxyphenylcarbonyloxy and p-n-hexadecyloxyphenoxycarbonyloxy), an amino group (preferable examples of the amino group include an amino group, a substituted or unsubstituted alkylamino group having from 1 to 30 carbon atoms, and a substituted or unsubstituted anilino group having from 6 to 30 carbon atoms, e.g., methylamino, dimethylamino, anilino, N-methylanilino and diphenylamino), an acylamino group (preferable examples of the acylamino group include formylamino, a substituted or unsubstituted alkylcarbonylamino group having from 1 to 30 carbon atoms, and a substituted or unsubstituted arylcarbonylamino group, e.g., formylamino, acetylamino, pivaloylamino, lauroylamino, benzoylamino and 3,4,5-tri-n-octyloxyphenylcarbonylamino), an aminocarbonylamino group (preferable examples of the group include substituted or unsubstituted aminocarbonylamino group having from 1 to 30 carbon atoms, e.g., carbamoylamino, N,N-dimethylaminocarbonylamino, N,N-diethylaminocarbonylamino and morpholinocarbonylamino), an alkoxycarbonylamino group (preferable examples of the alkoxycarbonylamino group include substituted or unsubstituted alkoxycarbonylamino groups having from 2 to 30 carbon atoms, e.g., methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n-octadecyloxycarbonylamino and N-methyl-methoxycarbonylamino), an aryloxycarbonylamino group (preferable examples of the ryloxycarbonylamino group include substituted or unsubstituted aryloxycarbonylamino groups having from 7 to 30 carbon atoms, e.g., phenoxycarbonylamino, p-chlorophenoxycarbonylamino and m-(n-octyloxy)phenoxycarbonylamino), a sulfamoylamino group (preferable examples of the sulfamoylamino group include substituted or unsubstituted sulfamoylamino groups having from 0 to 30 carbon atoms, e.g., sulfamoylamino, N,N-dimethylaminosulfonylamino and N-n-octylaminosulfonylamino), an alkyl or arylsulfonylamino group (preferable examples of the alkyl or arylsulfonylamino group include substituted or unsubstituted alkylsulfonyl amino groups having from 1 to 30 carbon atoms, and substituted or unsubstituted arylsulfonylaminogroups having from 6 to 30 carbon atoms, e.g., methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino, 2,3,5-trichlorphenylsulfonylamino and p-methylphenylsulfonylamino), a mercapto group, an alkylthio group (preferable examples of the alkylthio group include substituted or unsubstituted alkylthio groups having from 1 to 30 carbon atoms, e.g., methylthio, ethylthio and n-hexadecylthio), an arylthio group (preferable examples of the arylthio group include substituted or unsubstituted arylthio groups having from 6 to 30 carbon atoms, e.g., phenylthio, p-chlorophenylthio and m-methoxyphenylthio), a heterocyclic-thio group (preferable examples of the heterocyclic-thio group include substituted or unsubstituted heterocyclic-thiogroupshaving from 2 to 30 carbonatoms, e.g., 2-benzothiazolylthio and 1-phenyltetrazol-5-ylthio), a sulfamoyl group (preferable examples of the sulfamoyl group include substituted or unsubstituted sulfamoyl groups having from 0 to 30 carbon atoms, e.g., N-ethylsulfamoyl, N-(3-dodecyloxypropyl)sulfamoyl, N,N-dimethylsulfamoyl, N-acetylsulfamoyl and N-benzoylsulfamoyl, N-(Nxe2x80x2-phenylcarbamoyl)sulfamoyl), a sulfo group, an alkyl or arylsulfinyl group (preferable examples of the alkyl or arylsulfinyl group include substituted or unsubstituted alkylsulfinyl groups having from 1 to 30 carbon atoms, and substituted or unsubstituted arylsulfinyl groups having from 6 to 30 carbon atoms, e.g., methylsulfinyl, ethylsulfinyl, phenylsulfinyl and p-methylphenylsulfinyl), an alkyl or arylsulfonyl group (preferable examples of the alkyl or arylsulfonyl group include substituted or unsubstituted alkylsulfonyl groups having from 1 to 30 carbon atoms, and substituted or unsubstituted arylsulfonyl groups having from 6 to 30 carbon atoms, e.g., methylsulfonyl, ethylsulfonyl, phenylsulfonyl and p-methylphenylsulfonyl), an aryloxysulfinyl group (preferable examples of the aryloxysulfinyl group include substituted or unsubstituted aryloxysulfinyl groups having from 7 to 30 carbon atoms, e.g., phenoxysulfinyl, o-chlorophenoxysulfinyl, m-nitrophenoxysulfinyl and p-t-butylphenoxysulfinyl), an alkoxysulfinyl group (preferable examples of the alkoxysulfinyl group include substituted or unsubstituted alkoxysulfinyl groups preferably having from 2 to 30 carbon atoms, e.g., methoxysulfinyl, ethoxysulfinyl, t-butoxysulfinyl and n-octadecyloxysulfinyl), an aryloxysulfonyl group (preferable examples of the aryloxysulfonyl group include substituted or unsubstituted aryloxysulfonyl groups having from 7 to 30 carbon atoms, e.g., phenoxysulfonyl, o-chlorophenoxysulfonyl, m-nitrophenoxysulfonyl and p-t-butylphenoxysulfonyl), an alkoxysulfonyl group (preferable examples of the alkoxysulfonyl group include substituted or unsubstituted alkoxysulfonyl groups having from 2 to 30 carbon atoms, e.g., methoxysulfonyl, ethoxysulfonyl, t-butoxysulfonyl and n-octadecyloxysulfonyl), an acyl group (preferable examples of the acyl group include a formyl group, substituted or unsubstituted alkylcarbonyl groups having from 2 to 30 carbon atoms, and substituted or unsubstituted arylcarbonyl groups having from 7 to 30 carbon atoms, e.g., acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl and p-n-octyloxyphenylcarbonyl), an aryloxycarbonyl group (preferable examples of the aryloxycarbonyl group include substituted or unsubstituted aryloxycarbonyl groups having from 7 to 30 carbon atoms, e.g., phenoxycarbonyl, o-chlorophenoxycarbonyl, m-nitrophenoxycarbonyl and p-t-butylphenoxycarbonyl), an alkoxycarbonyl group (preferable examples of the alkoxycarbonyl group include substituted or unsubstituted alkoxycarbonyl groups having from 2 to 30 carbon atoms, e.g., methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl and n-octadecyloxycarbonyl), a carbamoyl group (preferable examples of the carbamoyl group include substituted or unsubstituted carbamoyl groups having from 1 to 30 carbon atoms, e.g., carbamoyl, N-methylcarbamoyl, N,N-dimethylcarbamoyl, N,N-di-n-octylcarbamoyl and N-(methylsulfonyl)carbamoyl), an aryl or heterocyclic azo group (preferable examples of the aryl or heterocyclic azo group include substituted or unsubstituted arylazo groups having from 6 to 30 carbon atoms, and substituted or unsubstituted heterocyclic-azo group having from 3 to 30 carbon atoms, e.g., phenylazo, p-chlorophenylazo and 5-ethylthio-1,3,4-thiadiazol-2-ylazo), an imide group (preferable examples of the imide group include N-succinimide and N-phthalimide), a phosphino group (preferable examples of the phosphino group include substituted or unsubstituted phosphino groups having from 2 to 30 carbon atoms, e.g., dimethylphosphino, diphenylphosphino and methylphenoxyphosphino), a phosphinyl group (preferable examples of the phosphinyl group include substituted or unsubstituted phosphinyl groups having from 2 to 30 carbon atoms, e.g., phosphinyl, dioctyloxyphosphinyl and diethoxyphosphinyl), a phosphinyloxy group (preferable examples of the phosphinyloxy group include substituted or unsubstituted phosphinyloxy groups having from 2 to 30 carbon atoms, e.g., diphenoxyphosphinyloxy and dioctyloxyphosphinyloxy), a phosphinylamino group (preferable examples of the phosphinylamino group include substituted or unsubstituted phosphinylamino groups preferably having from 2 to 30 carbon atoms, e.g., dimethoxyphosphinylamino and dimethylaminophosphinylamino), and a silyl group (preferable examples of the silyl group include substituted or unsubstituted silyl groups having from 3 to 30 carbon atoms, e.g., trimethylsilyl, t-butyldimethylsilyl and phenyldimethylsilyl).
Of the substituents mentioned above, those having hydrogen atom(s) may be further substituted by removing the hydrogen atom(s) and substituting the removed hydrogen atom(s) with any other substituent. The any other substituent may include aforementioned groups. Examples of the substituted substituents include an alkylcarbonylaminosulfonyl group, an arylcarbonylaminosulfonyl group, an alkylsulfonylaminocarbonyl group and an arylsulfonylaminocarbonyl group. Concrete examples thereof include a methylsulfonylcarbonyl group, a p-methylphenylsulfonylaminocarbonyl group, an acetylaminosulfonyl group, and a benzoylaminosulfonyl group.
When at least one of R1 and R2 is a substituent, the substituent is preferably a halogen atom, an alkyl group, an alkoxy group, cyano group or nitro group. More preferably, the substituent is ahalogen atom, an alkyl group oran alkoxy group.
Preferably, at least one of R1 and R2 is a substituent mentioned above other than a hydrogen atom. More preferably, both R1 and R2 are substituents other than hydrogen atom. In a case where both R1 and R2 are substituents mentioned above, it is preferable that each of R1 and R2 is independently a halogen atom, an alkyl group or an alkoxy group. Most preferably, both R1 and R2 are methyl groups.
In general formula (I), R3 represents a substituent. Examples of the substituent include those substituents mentioned above for R1 and R2. m indicates an integer from 0 to 3. When m is neither 0 nor 1, or that is to say, when m is 2 or greater, R3""s may be the same as or different from each other and may be bonded to each other to form a condensed ring. R3 may be bonded to R1 or R2 to form a condensed ring.
Preferably, R3 is an electron-attractive substituent having a Hammett""s substituent constant "sgr"p of no less than 0 (more preferably from 0 to 1.5). The Hammett""s substituent constant "sgr"p is described in detail in documents, for example, in Hamettosokuxe2x80x94Kxc3x4zxc3x4 To Han""nxc3x4sei (Hammett""s Rulexe2x80x94Structure and Reactivity) written by Naoki Inamoto (published by Maruzen); Shinjikken Kagaku Kxc3x4za 14, Yûki Kagxc3x4butsu No Gxc3x4sei To Han""nxc3x4V (Novel Experimental Chemistry Lecture 14, Synthesis and Reaction V of Organic Compounds), p. 2605 (edited by the Chemical Society of Japan, published by Maruzen); Riron Yûki Kagaku Kaisetsu (Theoretical Organic Chemistry Handbook) written by Tadao Nakaya, p. 217 (published by Tokyo Kagaku Dojin); Kemikaru Rebyû(Chemical Review), vol. 91, pp. 165-195 (1991).
More preferably, R3 is an electron-attractive substituent having a Hammett""s substituent constant "sgr"p of no less than 0.1 (more preferably from 0.1 to 1.5). Still more preferably, R3 is an electron-attractive substituent having "sgr"p of not less than 0.3 (more preferably from 0.3 to 1.0). Preferable examples of R3 include a halogen atom, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkoxysulfonyl group, an aryloxysulfonyl group, a sulfamoyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkoxysulfinyl group, an aryloxysulfinyl group, a carboxyl group, a sulfo group, a cyano group and a nitro group. More preferably, R3 is a halogen atom, an alkylsulfonyl group, an arylsulfonyl group, a sulfamoyl group, a cyano group or a nitro group.
In formula (I), R4 represents an aryl group or a heterocyclic group. Concretely, R4 represents an aryl group (preferable examples thereof include substituted or unsubstitutedaryl groups having from 6 to 30 carbon atoms, e.g., phenyl, p-tolyl, naphthyl, m-chlorophenyl, and o-hexadecanoylaminophenyl), or a heterocyclic group (examples thereof include monovalent groups derived from a substituted or unsubstituted, aromatic or non-aromatic heterocyclic compound preferably having 5 or 6 members heterocyclic ring by removing one hydrogen atom from the compound; examples of the hetero atom comprised in the hetero ring include nitrogen, oxygen, sulfur and phosphorus; more preferably, this heterocyclic group is a 5-membered or 6-membered aromatic heterocyclic group having from 3 to 30 carbon atoms, e.g., 2-furyl, 2-thienyl, 2-pyridyl, 2-pyrimidinyl, and 2-benzothiazolyl). R4 may have one or more substitutents. Examples of the substituent include the substituents mentioned above for R1 and R2. Preferably, R4 is an aryl group, and is more preferably substituted with ahalogen atom, an alkoxy group or an aryloxy group at an ortho-position thereof relative to an anilide nitrogen to which the R4 is bonded.
In general formula (I), R5 and R6 each independently represent a hydrogen atom or a substituent. Examples of the substituent for R5 and R6 include the substituents mentioned above for R1 and R2. Preferably, R5 and R6 represent substituents other than hydrogen atom, and more preferably represent alkyl groups. R5 and R6 may have one or more substitutents. Examples of the substituent for R5 and R6 include the substituents mentioned above for R1 and R2. More preferably, R5 and R6 each represent amethyl group, an ethyl group, a 2-hydroxyethyl group or a 2-methanesulfonylaminoethyl group.
In general formula (I), R7 represents a substituent. Examples of the substituent include the substituents mentioned above for R1 and R2. n indicates an integer from 0 to 4. When n is neither 0 nor 1, or that is to say, when n is 2 or greater, R7""s may be the same as or different from each other and may be bonded to each other to form a condensed ring. R7 may be bonded to R5 or R6 to form a condensed ring. R5 and R6 may be bonded to each other to form a ring. n is preferably 0 or 1, and is more preferably 1. R7 is preferably an alkyl group, an alkoxy group or an acylamino group, and is more preferably an alkyl group. More preferably, R7 is a methyl group that is ortho-positioned relative to an azomethine nitrogen in the compound represented by general formula (I). That is, R7 is preferably a methyl group that is provide at ortho-positione with respect to nitrogen of an azomethine portion in the compound represented by general formula (I)
Preferred examples of the compound represented by formula (I) of the present invention are shown below. However, the present invention is not limited thereto. 
In the following description, when the compound exemplified above is referred to, the compounds is designated as xe2x80x9cCompound (X)xe2x80x9d in which X indicates the parenthesized number of each compound.
The compound represented by general formula (I) can be produced through a coupling reaction of a compound represented by the following general formula (II) with an oxidation product of a p-phenylenediamine derivative, and more preferably with an oxidation product of an N,N-di-substituted p-phenylenediamine derivative.
General formula (II) 
In general formula (II), R1 and R2 each independently represent a hydrogen atom or a substituent; R3 represents a substituent; m indicates an integer from 0 to 3; when m is not 0 or 1, or that is to say, when m is 2 or greater, R3""s may be the same as or different from each other and may be bonded to each other to form a condensed ring; R3 may be bonded to R1 or R2 to form a condensed ring; and R4 represents an aryl group or a heterocyclic group. The details of R1, R2, R3, R4 and m are as described above for general formula (I). That is, the details of R1, R2, R3, R4 and m are the same as R1, R2, R3, R4 and m described for general formula (I).
Specifically, the dye represented by general formula (I) can be synthesized from a compound represented by general formula (II) and a compound represented by the following general formula (A), as shown below. Precisely, one hydrogen atom is dissociated from the compound represented by general formula (II), the compound is then coupled with an oxidation product of the compound (A), which has been oxidized with an oxidizing agent, and CO2 is removed from the coupled product to form an azomethine dye represented by general formula (I). 
In general formula (A), R5 and R6 each independently represent a hydrogen atom or a substituent; R7 represents a substituent; n indicates an integer from 0 to 4; when n is not 0 or 1, or that is to say; when n is 2 or greater, R7""s may be the same as or different from each other and may be bonded to each other to form a condensed ring; R7 may be bonded to R5 or R6 to form a condensed ring; and R5 and R6 may be bonded to each other to form a ring.
The details of R5, R6, R7 and n are as described above for general formula (I).
The compound represented by general formula (II) can be synthesized by various known methods. For example, it can be produced according to the methods described in examples described below.
The azomethine yellow dye compound of the present invention can be used as yellow dye for silver halide photographic photosensitive materials, yellow dye for inkjet or thermal transfer printing materials, yellow dye for toner in electrophotography, yellow dye for prints, yellow dye for color proofs, yellow dye for optical memory media, yellow dye for organic electroluminesence elements, filter dye for solid-state image pickup tubes or color liquid-crystal televisions, and as an intermediate used in the production thereof.
The azomethine yellow dye compound of the present invention has a large absorption coefficient, and color fastness thereof is good. Therefore, the dye compound is especially useful in image recording and has the merit such that an amount thereof to be used can be reduced as compared with conventional dyes. Accordingly, the dye compound is preferably used as yellow dye for silver halide photographic photosensitive materials, yellow dye for inkjet or thermal transfer printing materials, yellow dye for prints, and yellow dye for color proofs, and more preferable used as yellow dye for silver halide photographic photosensitive materials including color proofs and to yellow dye for inkjet or thermal transfer printing materials.